Convenient synthesis of optically active 1,2-diol monosulfonates and terminal epoxides via oxazaborolidine-catalyzed asymmetric borane reduction of α-sulfonyloxy ketones

被引:29
作者
Cho, BT [1 ]
Yang, WK [1 ]
Choi, OK [1 ]
机构
[1] Hallym Univ, Dept Chem, Chunchon 200702, Kangwondo, South Korea
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2001年 / 10期
关键词
D O I
10.1039/b010155i
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A very convenient asymmetric synthesis of 1,2-diol monosulfonates and terminal epoxides with high optical purity via oxazaborolidine-catalyzed asymmetric borane reduction of alpha -sulfonyloxy ketones using N-ethyl-N-isopropylaniline-borane complex as borane carrier has been developed.
引用
收藏
页码:1204 / 1211
页数:8
相关论文
共 79 条
[41]   IRREVERSIBLE AND HIGHLY ENANTIOSELECTIVE ACYLATION OF 2-HALO-1-ARYLETHANOLS IN ORGANIC-SOLVENTS CATALYZED BY A LIPASE FROM PSEUDOMONAS-FLUORESCENS [J].
HIRATAKE, J ;
INAGAKI, M ;
NISHIOKA, T ;
ODA, J .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (26) :6130-6133
[42]  
HOFFMAN RV, 1985, SYNTHESIS-STUTTGART, P760
[43]   RATIONAL DESIGN OF MN-SALEN EPOXIDATION CATALYSTS - PRELIMINARY-RESULTS [J].
HOSOYA, N ;
HATAYAMA, A ;
IRIE, R ;
SASAKI, H ;
KATSUKI, T .
TETRAHEDRON, 1994, 50 (15) :4311-4322
[44]  
Jacobsen E. N., 1993, CATALYTIC ASYMMETRIC
[45]   HIGHLY ENANTIOSELECTIVE EPOXIDATION CATALYSTS DERIVED FROM 1,2-DIAMINOCYCLOHEXANE [J].
JACOBSEN, EN ;
ZHANG, W ;
MUCI, AR ;
ECKER, JR ;
DENG, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (18) :7063-7064
[46]   PREPARATION OF ENANTIOMERICALLY ENRICHED COMPOUNDS BY USING ENZYMES .11. PREPARATION OF OPTICALLY-ACTIVE ALPHA-HYDROXY ACID-DERIVATIVES BY MICROBIAL HYDROLYSIS OF CYANOHYDRINS AND ITS APPLICATION TO THE SYNTHESIS OF (R)-4-DODECANOLIDE [J].
KAKEYA, H ;
SAKAI, N ;
SUGAI, T ;
OHTA, H .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1991, 55 (07) :1877-1881
[47]   MN-SALEN CATALYZED ASYMMETRIC OXIDATION OF SIMPLE OLEFINS AND SULFIDES [J].
KATSUKI, T .
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1995, 53 (11) :940-951
[48]   ALPHA-TOSYLOXYLATION OF ENOLIZABLE KETONES USING THALLIUM(III) PARA-TOLYLSULPHONATE (TTS) [J].
KHANNA, MS ;
GARG, CP ;
KAPOOR, RP .
TETRAHEDRON LETTERS, 1992, 33 (11) :1495-1498
[49]   A SIMPLIFIED PROCEDURE FOR THE STEREOSPECIFIC TRANSFORMATION OF 1,2-DIOLS INTO EPOXIDES [J].
KOLB, HC ;
SHARPLESS, KB .
TETRAHEDRON, 1992, 48 (48) :10515-10530
[50]   ONE-STEP ALPHA-TOSYLOXYLATION OF KETONES WITH [HYDROXY(TOSYLOXY)IODO]BENZENE [J].
KOSER, GF ;
RELENYI, AG ;
KALOS, AN ;
REBROVIC, L ;
WETTACH, RH .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (12) :2487-2489